He Loves His Little Meeskeit, But He Won’t Take Her Home to Mom

[Ed. note: this article was originally published on November 27, 1995.]

This is a story about a dirty little secret in the dating world. Almost everybody’s been there—on one side or the other.

Two men were sitting at the Princeton Club having drinks. It was late afternoon. Both men were in their early 30’s and had once been pretty-boy preppies who were now losing their looks. They had an extra 12 pounds around their middles that they couldn’t lose. They’d gone to college together and had moved to New York after graduation. They were good friends; they had the kind of friendship that tends to be unusual for men. They could actually talk about things. Like diets that didn’t work. And women.

Walden had just been made partner in a corporate law firm, and had recently gotten engaged to a dermatologist. Stephen had been in a relationship for three years. He was a producer on a network magazine show.

Walden’s fiancée was out of town at a collagen convention. On his own, Walden always got lonely. It reminded him of a time when he had really been lonely, for months on end that seemed to drag into years. And it always brought him around to the same memory, of the woman who had made him feel better, and of what he’d done to her.

Walden met her at a party filled with very pretty people. This being Manhattan, she was nicely dressed in a short black dress that showed off breasts that were on the large side. But she had a modest face. Beautiful long black hair, though. Ringlets. “They always have one great feature,” Walden said, and took a sip of his martini.

There was something about this girl, Libby. She was sitting on a couch by herself and she didn’t seem uncomfortable. Another girl came by, a pretty girl, and she leaned down and whispered something in Libby’s ear and Libby laughed. But she didn’t get up. Walden was standing by the side of the couch, drinking beer out of the bottle. He was thinking about which pretty girl to approach, looking for openings. Libby caught his eye and smiled. She looked friendly. He sat down, figuring it was a momentary oasis.

He kept thinking that he was going to get up and approach one of the pretty girls, but he didn’t. Libby had gone to Columbia undergrad, Harvard grad school. She talked to him about law. She told him about her childhood, growing up with four sisters in North Carolina. She was 27 and had a grant to make a documentary. She leaned forward and removed a hair from his sweater. “Mine,” said, and laughed. They talked for a long time. He finished a second beer.

“Do you want to come over to my place?” she asked.

He did. He figured he knew what was going to happen. They’d have sex for one night, he’d go home the next day and forget about it. Like most men in New York, he made up his mind about a woman right away. Put her in a category—one-night stand, potential girlfriend, hot two-week fling. Back then, he was sleeping with women and eventually there would be tearful scenes in his lobby and sometimes worse.

Libby was definitely a one-night stand. She wasn’t pretty enough to date, to be seen with in public.

“But what does that mean, really?” Stephen interrupted.

“I just thought she was uglier than me,” Walden said.

When they got to Libby’s apartment—a basic two-bedroom in a high-rise on Third Avenue that she shared with her cousin—she opened the refrigerator and took out a beer. When she bent over in the refrigerator light, he saw that she was a little on the heavy side. She turned around and unscrewed the cap and handed the bottle to him. “I just want you to know,” she said. “I really want to have sex with you.”

A pretty girl wouldn’t have said that, he thought, as he put down his beer and began undressing her. He bit her neck and pulled down the top of her bra without unhooking it. He peeled off her pantyhose. She wasn’t wearing underwear. They went into the bedroom.

“I found myself very uninhibited,” Walden said. “Because she wasn’t pretty. The stakes were lower; the emotion higher. There wasn’t any pressure because I knew I couldn’t date her.” He fell asleep with his arms around her.

“The next morning,” Walden said, “I woke up and felt at ease. Very relaxed. I’d been feeling tormented for some time and, with Libby, I suddenly felt peaceful. It was the first honest emotional connection I’d had in a while. So I immediately panicked and had to leave.”